I'd keep the 26 and get the LCP to go with it. I pocket carry LCP everyday/all day and it is great. The 26 will be easier to conceal vs the 19, but sometimes you wont want the weight... Like you mentioned, just taking out the trash, walking the dog, running to the store, etc. Being able to stash the 380 in the pocket has it benefits.

In the meantime, you could save up for the Glock 30. It's about the same size as the 19, but shoots the manly 45 ACP.... Not none of that dinky 9mm stuff

I went straight from the 26 to 30 and never looked back. I found the 30 is almost as easy to conceal IWB and throws a much better round.